The Documents sidebar displays a chevron (indicating subitems in a outline) only if the item’s child has children. It should show the chevron if the item itself has children. For example (note that my chevrons are shown as asterisk characters:
DOCUMENTS SIDEBAR
*MainDocument
*Lists
Item 1 (This item has children, but those items have no child items)
Item 2 (This item has children, but those items have no child items)
*Item 3 (This item has children, and at least one of those items has child items)
ACTUAL DOCUMENT CONTENTS IN OUTLINE VIEWER
MainDocument
—Lists
——Item 1 (Has child items, but no grandchild items)
———ChildItem 1
———ChildItem 2
——Item 2 (Has child items, but no grandchild items)
———ChildItem 1
———ChildItem 2
——Item 3 (Only this item is shown with a chevron in the Documents sidebar)
———ChildItem 1
————GrandchildItem 1
————GrandchildItem 2